Dichloromethane → HCID 86758194, compound

HRID 2186928Notes

Reaction equation

HRID 2186928 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[B].C(S)[CH2:13][CH2:14][SH:15].Cl[CH2:18]Cl>>[CH2:18]1[O:10][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)([CH3:9])[S:15][CH:14]1[CH3:13]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 80131,3-PropanedithiolHCID 8500p-METHYLACETOPHENONEHCID 5462311Boron

Product 1

HCID 86758194HCID 86758194, compound

Procedure

A solution of 4′-methylacetophenone (10 g, 74.5 mmol) and dichloromethane (200 mL) was treated dropwise with boron trifluoroetherate (12.5 mL, 104 mmol) at room temperature. To the resulting solution was added 1,3-propanedithiol (7.45 mL, 74.5 mmol) and the reaction mixture was stirred for 4 h at room temperature. The reaction was quenched carefully with saturated NaHCO3 solution and extracted with dichloromethane. The organic layer was separated and evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with 1 N NaOH, water, and saturated NaCl solution. The organic layer was separated, dried with MgSO4, filtered and solvent evaporated in vacuo to yield a crude oil. Purification of the crude oil via flash chromatography (50% CH2Cl2/hexane) afforded crystalline 4′-methylacetophenone propylene thioketal.

Workup

  1. customThe reaction was quenched carefully with saturated NaHCO3 solution
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with 1 N NaOH, water, and saturated NaCl solution
  7. customThe organic layer was separated
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. customsolvent evaporated in vacuo
  11. customto yield a crude oil
  12. customPurification of the crude oil via flash chromatography (50% CH2Cl2/hexane)

Sources & evidence

ORD record
ord-1989c6dc44454472a5953c04766e3022
Source dataset
uspto-grants-2002_06
Patent number
US06407136B1

Reaction notes

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